TY - JOUR
T1 - 1,3-Heterazolidin-2-ones as starting materials for optically active 1,3,2-oxazaborolines and 1,3,2-diazaboroline derived from ephedrines
AU - Cruz, Alejandro
AU - Geníz, Erika
AU - Contreras, Rosalinda
N1 - Funding Information:
A.C. is grateful for a scholarship from Conacyt-Mexico. Financial support was provided by Conacyt-Mexico. We thank Ing. Marco Leiva Ramı́rez for the X-ray diffraction determination.
PY - 1998/11/27
Y1 - 1998/11/27
N2 - (4R,5R)-3,4-Dimethyl-5-phenyl-1,3,2-oxazaboroline (la) derived from pseudoephedrine and (4R,5S)-1,3,4-trimethyl-5-phenyl-1,3,2-diazaboroline (1d) derived from ephedrine have been prepared from the corresponding 1,3- heterazolin-2-one. Hydrolysis of 1d afforded the 1-methyl-3-(methylamine)-2- phenyl-propylamine 5. The structures were established from 1H, 13C and 11B NMR data. The X-ray diffraction analysis of (4R,5S)-(+)-3,4-dimethyl- 5-phenyl-1-hydro-1,3-diazolidine-2-one (4e) was performed. Isomeric N- monoborane adducts of the 1,3,2-diazaboroline 1d were prepared, and their structures were deduced from the NMR data.
AB - (4R,5R)-3,4-Dimethyl-5-phenyl-1,3,2-oxazaboroline (la) derived from pseudoephedrine and (4R,5S)-1,3,4-trimethyl-5-phenyl-1,3,2-diazaboroline (1d) derived from ephedrine have been prepared from the corresponding 1,3- heterazolin-2-one. Hydrolysis of 1d afforded the 1-methyl-3-(methylamine)-2- phenyl-propylamine 5. The structures were established from 1H, 13C and 11B NMR data. The X-ray diffraction analysis of (4R,5S)-(+)-3,4-dimethyl- 5-phenyl-1-hydro-1,3-diazolidine-2-one (4e) was performed. Isomeric N- monoborane adducts of the 1,3,2-diazaboroline 1d were prepared, and their structures were deduced from the NMR data.
UR - http://www.scopus.com/inward/record.url?scp=0032573525&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(98)00428-5
DO - 10.1016/S0957-4166(98)00428-5
M3 - Artículo
SN - 0957-4166
VL - 9
SP - 3991
EP - 3996
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 22
ER -